The Mom Test (Part 2): Before, During, and After Customer Conversations — Stop Wasting Time Going Through the Motions

This post will walk you through:

How to prepare your questions: Using principles like the "Three Core Questions," "customer segmentation," and "dynamic updating" to ensure every conversation cuts straight to the point.
How to hear the truth: Asking questions that pass The Mom Test, so customers share their unfiltered, honest thoughts.
How to advance the customer: Seeking commitment at the end of a meeting so customers either walk away or genuinely become customers — rather than staying "forever prospects."
How to debrief the conversation: Extending value into the next conversation and closing the learning loop.
A complete structured process: "Pre-meeting preparation, in-meeting execution, post-meeting debrief" — reusable across every situation.

Pre-Meeting Preparation

Customer Segmentation

Why segment? Feedback only matters when it's consistent

Imagine using "students" as your target customer. In reality, these two people are both students:

A master's student in computer science at National Taiwan University, about to graduate
A sophomore studying business management at an Ivy League school

Startups often reach a consensus and dive straight into building a product or business without thinking twice.

This kind of vague segmentation creates one very important problem: inconsistent feedback.

You think you've done 20 customer conversations, but you've actually done 1 conversation with 20 different types of customers.

This prevents us from truly learning about customer pain points, making every effort futile — you're just spinning your wheels in a dead end.

But narrowing down your customer segment only requires a simple process:

Start with any group → Keep narrowing → Until you have

Someone specific you can talk to (Who)
A place you can find them (Where)

Then stop.

The core principle: Can you locate your customers with a clear physical or online address?

During the detailed segmentation process, you must pay attention to the following:

Within this group, who would want this most?
Will everyone in the group buy or use it, or only a small subset?
Why would this subgroup want this product? (For example: what is the specific problem?)

Once you've identified a few concrete "person + place" combinations, prioritize based on these three factors:

Potential profitability or market size
Ease of access
Which feels most rewarding or valuable to you

Now the task is to actually go find them, start conversations, and begin moving your business forward.

Bad segmentation: People who currently or may someday need to prepare for an English job interview

This is a classic example of how a broad segment traps you in several pitfalls:

You can't find anyone to talk to, or there are too many candidates to know where to start
You can't collect consistent feedback
You can't evaluate whether your solution succeeded or failed, because each subgroup has different needs and pain points

This is entirely normal — a fresh graduate and an engineer changing careers simply have different needs.

Good segmentation: Business management graduating seniors from NTU or NCCU aiming for top multinationals like FMCG firms, findable in Facebook groups and Dcard's job-hunting boards

Who can you talk to?

Business school students (business administration, international business, finance, etc.) at NTU and NCCU who are about to graduate.

Where can you find them?

Online: Facebook groups, Dcard's job-hunting boards
In person: consulting clubs, recruitment fair venues, etc.

Potential profitability or market size:

This group is generally willing to pay more to gain a competitive edge in landing high-paying industries. The total number is smaller than "everyone who needs to prepare for an English interview," but the value density within the segment is very high.

Ease of access:

By posting in online groups or attending offline recruitment events, you can easily reach dozens — or even hundreds — of precisely targeted customers. The channels are clear and the execution difficulty is low.

Most rewarding or valuable to you:

If you have a relevant background yourself, or you're passionate about helping Taiwan's top talent step onto the world stage, this group will give you a strong sense of fulfillment.

Once you've locked in this well-defined customer segment, the feedback you receive will be remarkably consistent. Their pain points are likely to revolve around things like "I can't find anyone to practice case interviews with," "I don't have access to up-to-date interview information," and "I want to hear how seniors who succeeded actually did it."

With your target segment defined, it's time to decide what you actually want to learn from them.

Define Your Three Core Questions

What are the Three Core Questions? The key things your team actually wants to understand

The core spirit is very simple:

"What do we want to learn from these people (potential customers)?"

If you don't even know what you want to learn, the conversation is essentially a waste of time.

The number "three" is just a convenient guideline to follow. What matters most is keeping the conversation focused and avoiding the trap of going through the motions.

If you have a founding team, take note:

The entire team should be involved in preparing the Three Core Questions — including sales, product, and everyone else.

We need to make sure the customer conversation covers everyone's concerns and the assumptions each person wants to validate.

The D Question: At least one question must have the potential to completely destroy your idea or business

A question with the potential to destroy your idea or business is critically important.

Startups often end up building:

"A product nobody in the market wants"
"A product whose alternatives are already good enough"
"A product that's technically impossible to build right now"

Having this kind of question lets us pull back from the edge before we drive into a dead end, and identify where the real pain points actually lie.

Discovering that an idea is fundamentally flawed is demoralizing, but you can take what you've learned — and even shift the focus to a new pain point right there in the conversation.

Failure = learning that brings you one step closer to success

Example exercise: Three Core Questions for an English interview simulator

Using an English interview simulator as an example, the Three Core Questions we might prepare could be:

The actual interview preparation process:

Question: Is there anything about how you prepare for interviews that we wouldn't know just by guessing?
Purpose: To understand the actual workflow, and not focus too early on the pain points around verbal practice itself (what our product offers).

Which stage matters most:

Question: In the entire job search process, which stage do you think is most important — polishing your resume, applying for roles, or preparing for interviews?
Purpose: To find out how much the user prioritizes "preparing for English interviews." If this is far less important to them than "finding more job openings," then our product is just a nice-to-have, not a must-have.

Whether they've paid for any tools (the D Question):

Question: The last time you were preparing for a job search, how much time or money did you spend? Would you be willing to walk me through a specific experience?
Purpose: If the answer is "I didn't spend any money — I just read some articles online," this may indicate that the problem isn't painful enough to justify paying for a solution. In other words, this might not be a business problem worth solving at all.

Respect each other's time: Five minutes of pre-research

While preparing your questions, you'll notice that a few of them could be answered with a quick search.

If you can get the information from Google, then Google it.

Respect the precious time you both have — don't waste the conversation on obvious facts that are readily available online.

Define Your Next Steps

Prepare to advance

At the end of the conversation, in addition to gathering the key things we wanted to learn, we should also be pushing for the next step.

This "next step" doesn't have to be a signed order — it can be any form of commitment, such as:

Time commitment: "We'll have a new version next week. Would you have 15–20 minutes for an online call to try it out and give us some direct feedback?"
Network commitment: "Besides yourself, who else do you know who feels most strongly about the job search experience? If it's convenient, would you be willing to make a quick introduction for us?"

A meeting with no next step = a meeting with no meaning

Never say "I'll think about it and get back to you." Plan your advance move ahead of time.

Our goals are:

During the conversation: learn from the customer
After the conversation: filter for genuinely interested customers and push the business forward

Once you've segmented your customers, prepared your Three Core Questions, and decided on your next steps, you're ready to enter the conversation.

In-Meeting Execution

The optimal setup: Two people, one team

The ideal setup for customer conversations is a pair:

One person focuses entirely on talking; the other focuses entirely on taking notes.

The biggest problem with a solo interview is that you can't tell when you've gone off track.

This is where the note-taker can step in to redirect the meeting back to what matters (the Three Core Questions), rather than letting the conversation get swept away by subjective emotion or minor tangents.

Efficient note-taking: Capturing key signals

With AI note-takers, do you still need to take notes?

In today's environment, using AI to record and summarize meetings has become the norm.

This is a good thing — it lets us:

Keep a complete record, including emotions, context, and other important information.
Get a real-time summary with all the key points at a glance.

But this depends on both parties agreeing to be recorded — which immediately breaks the "keep it casual" illusion.

If you understand The Mom Test's concept, you know that not every customer conversation starts as a formal online meeting.

Given this reality, we still need to learn a few efficient note-taking methods so we're always ready to capture what matters.

Key elements: Quotes, emotions, names, blockers

Quotes

Record what was said verbatim using quotation marks whenever possible

Emotions

Common symbols:
- :) happy
- :( angry
Any strong emotion is worth recording.
"This is a problem." carries entirely different meaning depending on whether it's said neutrally or with anger.

Names

Record specific names, company names, etc.
If the person knows them → ask at the end whether they'd be willing to make an introduction (advance)
If it's a competitor or an alternative solution → research it afterward

Blockers

Even though a customer wants to solve a problem, these "blockers" prevent them from doing so
Record these blockers and think about whether your idea can realistically address them.

What should you take notes on?

If it's a formal meeting, a laptop is the best choice. It saves you the hassle of transcribing later.

If the conversation happens unexpectedly, a pen and any writable surface is the best option.

A napkin
A tissue
A pocket notebook

Rather than trying to remember all the important details, write down what was said on whatever surface you have at hand.

Finally: Make sure your notes are permanently saved and always accessible

Notes are useless if you never read them.

Take a photo of your notes, organize them in Notion, and use AI to generate a summary.

Today's tools spare us from many tedious steps — we no longer need to manually type up handwritten notes.

Make storing your notes the first priority. Ideally, get them into a trusted system immediately.

You'll regret it deeply when you can't remember that brilliant quote you wanted to put on your website.

What if you realize mid-meeting you're not solving a good problem?

This is actually a great opportunity:

Pull out another sheet of paper
Write down the new problem the customer just surfaced for you
This new problem is typically already validated

It's your perfect moment to pivot out of the dead end!

Seeking commitment and advancing the customer

As the meeting naturally winds down, you've already gathered the information you came for.

But that's not enough — our core goal is always to "advance."

What "advancing" means is: the customer will choose to leave or become a customer. Both outcomes are valuable learning results.

Like a funnel, by giving customers a clear opportunity to say no, you filter them into:

Customers who are genuinely interested
Prospects who feel positive but will never actually buy

People stop lying to you when you ask for their money.

The point is to make customers put something on the line, and from that, either move the business forward or receive a strong negative signal.

Not every advance will succeed — but if you always let meetings end as "meetings that felt pretty good," that's the real failure.

Post-Meeting Debrief

Team review of notes together

After the conversation ends, the first step is to immediately organize your notes and share them with the entire founding team.

Whether you use an automated tool to transcribe a recording and generate a summary, or simply paste your handwritten notes into a shared document — either works.

What matters is being "immediate" and "transparent."

We need the whole team's participation, because product, marketing, and technical perspectives are all different. Miss any one of them, and you may overlook the key concerns from that angle.

Then open it up for everyone to have an asynchronous discussion on the notes:

Highlight the gold: Mark the "golden quotes" or unexpected perspectives that made your eyes light up.
Raise questions: Flag answers that were unclear, or places where you suspect there may be a misunderstanding.
Add perspective: From your own area of expertise, add your interpretation of what the customer said.

This process ensures we're not making decisions based on a single point of view, but on the collective intelligence of the team.

Dynamically update your plan and Three Core Questions

With everyone's input in hand, you can now update based on what you've learned:

Beliefs: Did this conversation validate one of our beliefs, or overturn it? Does our understanding of the market need adjusting?
Three Core Questions: What did we learn from these people? What do we still want to learn?

Through this process of dynamic updating, your startup direction stops being built in an echo chamber and instead evolves iteratively through every real collision with the market.

Review the conversation itself

Finally, we also need to look back and evaluate "the conversation itself." Customer interviews are a craft — they only improve through deliberate practice.

Discuss together:

Quality of questions: Which questions led to deep, revealing answers? Which only produced surface-level responses? How can we ask better questions next time?
Success of the advance: Did we successfully secure a commitment at the end of the meeting? If not, where did things go wrong? Were we afraid to ask, or did we propose the wrong kind of "cost"?
Emotions and atmosphere: How was the overall tone? Did we make the other person feel relaxed and willing to share? Or were we too leading, making them want to just tell us what we wanted to hear?

Reviewing conversation technique ensures that each subsequent interview is higher quality, uncovering more authentic and valuable information.

Hidden technique: The first conversation doesn't have to be a "meeting"

Suppose you already have a startup idea — or even a product.

Then congratulations: you can have a customer conversation at any time!

Who should you talk to?

In the early stages, the range of people you can talk to is broad, for example:

Industry veterans: If you have access, they can provide a macro-level perspective.
Potential customers: They are the frontline validators of whether the problem actually exists.

But the key is "how" you open that conversation.

Many people's first instinct is to "set up a coffee chat," but this is actually a trap.

That framing already implies "I might be wasting your time," which puts the other person on guard immediately and makes the dynamic of the conversation unequal.

If you feel like the other person is "doing you a favor," then the conversation is already too formal.

Turn an "interview" into a "conversation"

The best customer conversations happen in the most natural circumstances.

Rather than scheduling something deliberately, create opportunities for organic encounters:

Actively attend industry events.
Host small gatherings like an HR meetup.

In these settings, people are more open-minded and far more likely to fall into a relaxed, natural exchange.

Approaching a stranger might feel strange to you — but that usually only happens when you're treating it like an "interview." If you genuinely treat it as just a "conversation," everything becomes completely natural.

The golden rule of conversation

In these informal conversations, you don't even need to explain why you're there or mention that you're building a startup.

The only thing you need to do is take a genuine interest in their life and their problems.

As long as you're willing to truly listen to someone else's problems, you're already more interesting than 99% of people.

Remember: never mention your idea during the conversation unless you're already prepared to "advance" to the next step and ask for a commitment.

In the early stages, your goal is to learn, not to sell. If you need an excuse, "collecting data for a research project or paper" is the ultimate all-purpose cover story. This reason gives your questions an innocuous framing that makes people far more willing to share their real experiences rather than politely tell you what you want to hear.

Customer Conversation Cheat Sheet

If you prefer a quick-reference list:

Core mindset: Keep it casual

Conversation, not a meeting: Learn in the flow of natural exchange.
Avoid "setting up a coffee chat": It puts people on guard.
Create organic encounters: Attend industry events and join relevant communities.
Stay focused on the other person: Hold genuine curiosity about their problems.
Learn first, don't sell: Never mention your idea unless you're ready to advance.

1. Pre-Meeting Preparation

Precise segmentation: Define who your customers are (Who) and where to find them (Where).
Set your Three Core Questions: Focus your learning goals, including one "D Question" that could destroy your business.
Design your next step: Plan the "commitment" you'll seek (time, reputation, money).

2. In-Meeting Execution

Go in pairs: One person leads, one takes notes — and pulls things back on track when needed.
Take efficient notes: Capture only key quotes, emotions, names, and blockers.
Seek commitment: At the meeting's end, boldly propose the next step and use "cost" to gauge real interest.

3. Post-Meeting Debrief

Share notes with the team: Do it immediately, and get everyone involved in the discussion.
Update dynamically: Based on new information, update the team's core beliefs and Three Core Questions.
Review conversation technique: Debrief the quality of your questions and your advance attempts — and keep improving.